2,4,6-Trichloroanisole

2,4,6-Trichloroanisole
Names
	Preferred IUPAC name 1,3,5-Trichloro-2-methoxybenzene
	Other names 2,4,6-Trichloroanisole; TCA; 2,4,6-Trichloromethoxybenzene
Identifiers
CAS Number	87-40-1 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:19333 ;
ChemSpider	6620 ;
ECHA InfoCard	100.001.585
EC Number	201-743-5;
KEGG	C11510 ;
PubChem CID	6884;
RTECS number	MFCD00000588;
UNII	31O3X41254 ;
CompTox Dashboard (EPA)	DTXSID9073886 ;
	InChI InChI=1S/C7H5Cl3O/c1-11-7-5(9)2-4(8)3-6(7)10/h2-3H,1H3 Key: WCVOGSZTONGSQY-UHFFFAOYSA-N ; InChI=1/C7H5Cl3O/c1-11-7-5(9)2-4(8)3-6(7)10/h2-3H,1H3 Key: WCVOGSZTONGSQY-UHFFFAOYAT;
	SMILES COc1c(Cl)cc(Cl)cc1Cl; Clc1cc(Cl)cc(Cl)c1OC;
Properties
Chemical formula	C7H5Cl3O
Molar mass	211.47 g·mol−1
Melting point	60 to 62 °C (140 to 144 °F; 333 to 335 K)
Boiling point	140 °C (284 °F; 413 K) at 28 Torr
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H319, H413
Precautionary statements	P264, P270, P273, P280, P301+P312, P305+P351+P338, P330, P337+P313, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

2,4,6-Trichloroanisole (TCA) is a chemical compound that represents one of the strongest of off-flavors, substances "generated naturally in foods/beverages [that considerably] deteriorate the quality" of such products. As of 2000, TCA was considered the primary chemical compound responsible for the phenomenon of cork taint in wines, and it has an unpleasant earthy, musty and moldy smell.

Chemically, TCA is a chlorinated derivative of anisole, and it is a formed by the biomethylation of 2,4,6-trichlorophenol. More generally, it may be produced when naturally occurring airborne fungi and bacteria are presented with chlorinated phenolic compounds, which they then convert into chlorinated anisole derivatives. Species implicated include those of the genera Aspergillus, Penicillium, Actinomycetes, Botrytis (e.g. Botrytis cinerea), Rhizobium, or Streptomyces.

The chlorophenol precursor, 2,4,6-trichlorophenol, is used as a fungicide; more generally, related compounds can originate as contaminants found in some pesticides and wood preservatives, or as by-products of the chlorine bleaching process used to sterilize or bleach wood, paper, and other materials.

TCA has also been suggested as cause of the "Rio defect" in coffees from Brazil and other parts of the world, which refers to a taste described as "medicinal, phenolic, or iodine-like". In investigation of the mechanism of its role in producing off-flavor effects, it was found to "attenuate olfactory transduction by suppressing cyclic nucleotide-gated channels, without evoking odorant responses."

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